


The Family Business

by N7Biotic223, XxAngelicMurderxX



Category: Undertale (Video Game)
Genre: 1940s, Adult Content, Adult Frisk (Undertale), Alternate Universe - Mob, Alternate Universe - Mobtale (Undertale), Bara Sans (Undertale), Blood and Violence, Complicated Relationships, Crimes & Criminals, Death, Drama, Drama & Romance, Everyone Has Issues, Everyone Needs A Hug, F/F, F/M, Family Drama, Female Frisk (Undertale), Fluff and Smut, Frisk (Undertale) Is a Sweetheart, Gang Violence, Gun Violence, M/M, Mental Health Issues, Mental Instability, Organized Crime, POV Third Person, Prejudice Against Monsters (Undertale), Protective Sans (Undertale), Psychological Drama, Relationship(s), Slow Burn, Strippers & Strip Clubs, Triggers, Undertale Monsters in Heat, Undertale Monsters on the Surface
Language: English
Status: In-Progress
Published: 2019-06-18
Updated: 2020-01-18
Packaged: 2020-05-14 06:27:23
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 7
Words: 14,529
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19267666
Author URL: https://archiveofourown.org/users/N7Biotic223/pseuds/N7Biotic223, https://archiveofourown.org/users/XxAngelicMurderxX/pseuds/XxAngelicMurderxX
Summary: Frisk always dreamed of one day joining the family business. She always wanted to follow in her father's footsteps, even if the family business isn't the most...legal thing. While her father is reluctant to let her join such a risky business, he finally gives in once she turned 20 and puts her well being in the hands of his most trusted job men, Sans and Papyrus. With them by her side, she learns just how dangerous the world she desperately wanted to be apart of really is.





	1. Humble Beginnings

**Author's Note:**

> It's been 2 years since I finally wrote something and published it here, but I'm glad to be back, even just a little bit. I want to take a moment to thank all the amazing people who read, commented, and kudo my past work and hope that this one will live up to the works of the past. This is a darker set up then my previous works, so I will place a trigger warning in effect. While this first chapter shouldn't have too much to be concerned about, later chapters will get very dark and intense. I will also be updating tags as the story goes to let people know what all the story contains as it goes on. I hope you like it!
> 
> Important note: I am currently working on a book I one day hope to have published so chapters might be uploaded in a decent amount of time between each other since I don't want to burn myself out on either projects. I hope you don't mind the wait in between chapters because I plan on making them worth it! Thank you for reading and please enjoy the first chapter of The Family Business!
> 
> Shout out to XxAngelicMurderxX for helping me made this fic into a reality!

     Black clouds stormed in the sky, thunder roared, and freezing cold rain fell to the ground with no end in sight. The trash and dirt that littered the streets washed away down into the storm drains, but no amount of rain could ever make the streets clean. Crime and violence was at a all time high. Everyday, it seemed more and more people were turning into criminals. The mafia families were at the peak of power, taking over the city faster then anyone could of predicted. The police had given up trying to stop these families, turning a blind eye to all their crimes for the right price, except for drugs of course. Prostitution, blackmailing, and murder was fine for the right price, but drugs was where the line was drawn. Things got even more intense when a monster family started to gain some territory in the already crime ridden city, encouraging more monsters to leave the underground where they hid for countless years. People could not even tolerate their own kind over minor differences. How could monsters ever hope to make it in a human world where it was kill or be killed among their own people? Only time could tell, but nonetheless, another family, a monster one at that, joining the ranks in a already desperate city would only make things worse. Blood will run down the streets in a tidal wave of death and violence. While they played their games, the innocent and honest will take the hardest blows, but that's just how the game goes. The honest lived hard lives, barely able to pay for their protection fees, let alone their bills and rent. More honest people were forced to turn to a life of crime just to keep themselves from drowning. Some families were even forced to make sacrifices. Sometimes, the kids had to go. Some tell themselves that their kids will find better families and in some cases, it was true, but there were the unfortunate souls that never got a chance. Not even the orphanages that promised to take good care of the children in their homes would not give them a chance, killing their chances of normality before their lives even started. 

     The freezing rain chilled her down to her very soul. Not even the thin, worn out clothes the orphanage gave her helped keep the cold off of her. Her fresh cuts stung harshly and she felt sore. Her body shook violently from the cold, the rain and wind making her pain even harder to deal with. Anything was better then that place though. She'd rather be cold, hungry, and hurt then spend another moment in that horrible place. The ally did little to protect her from the elements, but it at least helped with the pain in her back. Her back only burned now, but at least it wasn't as cold as the rest of her was, even if it wasn't by much. Tears streamed down her face as the little girl pulled her knees close to her chest and rested her forehead against them. She didn't know what would happen to her or how long she would last like this, but she'd rather die here in the cold then in the hell she had been placed into. All she knew was that her body was freezing and on fire all at once and her eyes were getting heavy with each passing moment. She fought to keep her eyes open, terrified if she fell asleep now that she would never open them again. However, it was a losing battle and soon enough she was plunged into darkness with nothing but ice and fire surrounding her body with the sound of rain slowly lulling her to sleep. 

     Then, a sweet motherly voice broke the sympathy of the rain. At first, she didn't understand what the voice said. She didn't have the strength to open her eyes to look at the voice's origin. Besides, it was more likely a voice that had nothing to do with her. It wouldn't be the first time someone walked past a troubled soul without a regard for them. That was something she wasn't a stranger to. However, the voice started again, this time with a much deeper voice accompanying it. While the first voice was sweet, the second one was far deeper, almost booming, but still sounded kind. This time though, both voices sounded closer and had a hint of panic in them. The sound of rushing footsteps came towards her, not past her, but towards her. She slowly lifted her head and forced her tired eyes to open just wide enough to see what had came to her. When her vision cleared up, she was shocked to see a goat woman with a pair of small horns on her head and wide, concerned eyes. Her fur was snow white and looked soft to the touch. She faintly noticed that her fur looked dry for the most part, but now was quickly getting soaked by the rain. Along with her fur, the goat woman's tan dress was getting wet as well. She could see the dress wasn't cheap, but not overly expensive either. It was short sleeved, buttoned at the chest, and had a cloth that wrapped around her waist and tied into a knot in the front. Even though she was shocked to see a goat woman in front of her, she had no strength to react beyond her eyes opening just a bit wider. Frisk remembered all the stories the other kids told her about monsters. That they would eat her when they got the chance or rip her apart, and when she saw the woman's claw coming for her, she expected the stories to be true. However, she was shocked when no pain sheered through her body. No claws ripped into her flesh. The woman put her large, clawed, paw on her cheek. Her touch was so tender and soft. She hadn't felt someone touch her so gently in years that the simple gesture was enough to make her want to cry even harder. 

     "Oh my...", she whispered softly, just loud enough for her to hear the woman's words. 

     "Poor thing...", the second powerful voice spoke, surprising her again when she finally noticed who the second voice belonged to.

     Standing impossibly tall behind the goat woman was a goat man. His horns were much bigger then the woman's and a mane of golden hair around his head and face reminded her of a lion. He was huge and wide, yet, his eyes showed sadness and just as much tenderness and care as the woman's did. The man wore a tight fitting black and striped suit, white undershirt, and red tie. On the right side of his chest there was a pocket with the edge of a cloth showing itself. In one massive paw, he held the umbrella she assumed the woman abandoned. His sheer size was enough to intimidate even the biggest human, but he didn't seem like a scary man. He strangely seemed gentle despite his massive size. 

     "We can't leave her here...", the woman spoke again, looking behind herself to the man before looking back at her again. 

     Frisk suddenly felt the woman's arms wrap around her small body, gently picking her small body up off the ground. She expected to feel her cuts sting her the moment the monster grabbed her, but she felt nothing. She barely even felt cold anymore. Frisk watched as the man pulled out a brick like phone out of his suit and started calling someone. Who, she couldn't tell. His voice became background noise as he held the umbrella over the woman as she held Frisk, finally feeling the rain no longer falling on her skin. Her weak eyes looked up at the woman as she felt her body being held tightly in a hug like embrace, up against the woman's warm chest.

      The woman whispered the most comforting thing she's ever heard just as she felt herself losing consciousness, "You're going to be okay. We'll take care of you."

 

 

 

     When Frisk woke up again, she was in a soft bed with a wet rag on her forehead. It was a room she didn't recognize, but it was a place that she had dreamed of. A nice warm bed, books, toys, everything a child could ever want. She thought that this was all a dream and any minute now she would wake up back in the cold, damp room of the orphanage in a hard bed, but it was too real to be a dream. Frisk tried to sit up but it hurt to do it. That's when she realized that her old rags for clothes were replaced by a blue and purple sweater dress. It was nothing like she's ever seen before and softer then anything clothes she's ever worn before. Did the goat lady make it herself? When she lifted the blankets a little, she pulled her dress up a little to see that the cuts on her side had been bandaged. Frisk let the blanket down as confusion rushed through her. Did those people...bring her home and patched her up? 

     She wouldn't have to wonder for long. The door to her room opened and a little goat boy walked through with a plate with a bowl on it in his paws. He oddly looked a lot like the goat woman with a pair of pretty eyes, but he had some tiny details that reminded her of the goat man as well. He didn't have any horns yet, but maybe because he wasn't old enough to grow them yet. He looked a couple of years older then her, maybe eight, but no older then ten. He was dressed in a sweater similar to her's, but colored green and yellow instead with a pair of shorts. When he looked towards her, a little smile grew on his face.

     "Oh, you're finally up!", he happily spoke to her before walking deeper into the room and placing the plate down on the end table near her.

      He looked at her curiously, but happily and spoke again, "Mama, wanted me to bring you some soup hoping you'd be awake now. She'll be so happy to see you're up. She was really worried about you. She said you had a really bad fever."

     "Your mom isn't scared of getting you sick?" Frisk asked, her voice weak, but just strong enough to get the words out without much of a struggle. 

     "She says I don't have to worry because monsters don't get sick as easily as humans do.", he explained, "My name's Asriel."

     She smiled softly, "My name's Frisk."

     He looked at her a bit strangely, "Frisk? That's a odd name, but I like it! I hope we can be friends and play together when you get better!"

     Frisk smiled a little bigger from his words, "Yeah, me too..."

    

     

     Asriel was sweet and visited her often after that. While she wasn't strong enough to talk for long periods of time, he talked plenty for the both of them, but Frisk didn't mind it. It was actually really nice to have someone to talk to that was nice to her, even if she didn't do much talking. Asriel and her became friends quickly. She found out it was Asriel's bed she was sleeping in, but because his dad wasn't home often, he was able to sleep with his mom while she got better and he didn't seem to mind letting her use it either. His mother, whose name she found out was Toriel, came to see her a lot too. Toriel gave her medicine, made sure she ate at least a little bit every day, and helped her whenever she needed something. Frisk never could remember anyone who treated her so kindly. Toriel and her son seemed quite fond of her and even the man, who she found out his name was Asgore, seemed to really like her despite being gone most of the time. She really liked being here. She finally felt safe and loved. Frisk feared that once she got better that they would take her back to the orphanage, not knowing just how bad it really was. The orphanage convinced her that nobody would want her. That she would live there forever until she was an adult or until something very bad happened to her. It was always a fear that one day Toriel would come in and tell her they were going to send her back to that place.

     One day, Toriel came to check on her and asked the question she was terrified of hearing. "Do you have a family?"

     Frisk didn't want to lie to the woman who treated her so kindly. It wasn't fair to her, so even with fear rising in her chest, Frisk simply shook her head.

     "Oh poor dear...", she sweetly spoke, gently stroking her short brown hair. 

      Toriel was quiet for a moment before finally speaking with a smile and warmth in her eyes, "Well...Asgore and I have been talking and...we would love to have you as our daughter."

     The words surprised Frisk so intensely that her eyes widened and she froze, staring at the goat woman, unable to believe what she was saying to her. 

     "R-really? Me? Your...daughter?", she asked with her voice starting to shake and her eyes starting to water up.

     Toriel nodded softly before saying, "What do you say?"

     Frisk practically leap out of bed and hugged Toriel tightly, tears running down her face, "Yes!"

     Toriel hugged her new daughter tightly and nuzzled her sweetly, whispering, "Welcome to the family Frisk."

 

     She never thought this day would come. A family actually wanted her. Asriel was going to be her brother, Toriel her mother, and Asgore, though often absent, would be her father. It was everything she ever dreamed of. While she never expected a monster family would be the one to take her in, she wanted it more then anything nonetheless. She loved them all and they loved her back. As she cried tears of happiness into her new mother's chest, Frisk finally felt happiness. Never did she ever expect that she had just entered into a family that was much bigger then expected, she also didn't expect the unimaginable to happen. 


	2. Him

     The morning’s first rays of sunlight peeked their way into Frisk’s room, slowly waking the human girl reluctantly. A soft groan left her lips as Frisk pulled the blankets over her head, trying to keep herself from waking so early, but it was already too late. She could already feel her body coming to life and knew that going back to sleep wasn’t in her future. Reluctantly, she sat up and stretched bringing forth a yawn as she did. Her short brown hair was a mess and her eyes hurt. After rubbing one of her aching eyes, Frisk instinctively looked to the other side of the room. Every day she expected see another bed in her room, but it wasn’t all that long ago since she moved into her own room. It’s been a long time since she’s seen him though.

     Frisk smiled sadly at the thought of him. She thought they would be partners in crime forever, but that all changed when he disappeared. No one can say when or how it happened, but Asriel just…vanished. Frisk had spent a lot of time with him by then, several years actually, but it’s been several years since she’s seen him too. Nobody knows what happened. No even dad’s best informants could tell him anything. Asriel went outside one day and never came home. Her heart ached thinking about him. Asriel was everything to her. The moment Frisk became his sister, he promised to be the best big brother he could be and up until he disappeared, he kept that promise. She couldn’t remember how many times he made her smile and laugh. He was there to be her shoulder to cry on. Then, he just wasn’t there anymore. The fact no one had a clue what happened to him made the pain harder to deal with. There was nothing to give them hope or closure and there probably never will be.

     Despite moving into her own room since her old room held nothing but painful memories, Frisk still often looked across the room expecting to see Asriel sleeping or waking up her up with a bright smile on his face. They were only fourteen when he disappeared. Life hadn’t even really started for either of them. That was when she found out about the family business too. Her whole world shattered with her brother’s disappearance. Everything she knew was shattered. At the same time though, it also answered a lot of questions. Why was dad busy all the time? Why did mom insist on home schooling us? Why did everyone who came to the house always looked professional? Mom told her for years that dad was a business man and for a long time Frisk bought it. However, when Asriel disappeared, Frisk found out that mom didn’t lie to her, but never once told her that he was the Don of the only monster mafia in the city.

     Frisk felt no anger at her family; especially when they sat down to talk her about it. She was confused and shocked at first, but never angry. After all, they were good to their children. Asgore was an amazing dad when he was home and Toriel was the best mother she could ever hope for. They hadn’t even really told Asriel the full truth either, so it wasn’t like they were just hiding things from her. Asgore was serious the entire time they talked about it and extremely nervous to see how his daughter would react to such news. He wanted to be completely honest with her, even if he ruined the image she had of him. Asgore made it clear that they did bad things, just not to the same extent as human mafias went. They killed only when they needed to and protection fees were very reasonable if there was any at all. He confessed that he had blood on his hands himself, but did what he needed to in order to protect the family, both blood, adopted, and business wise.

     She didn’t hate him, if anything, she understood him. Frisk didn’t like the idea of killing, but understood doing it when no other choice was there. Besides, after everything her mother and father had done for her…how could she ever hate them for anything? Even if they were involved in a shady business, she knew they were good people. They took her in when no one else would and treated her like she was the real daughter. Even after their son disappeared, there was sadness in their eyes, but they never stopped loving her and taking care of their remaining child. They even told her about the business to protect her, to make her aware that…people might come after her too. They suspected some rival gang or something took Asriel given who his parents were and decided it was time to tell Frisk everything for her well being. Never did they suspect that telling her everything would make her want to be a one of them.

     With a soft sigh Frisk tried to push all those thoughts aside as she forced herself to get out of bed. Once she was standing, Frisk stretched one more time before making her way to her closet to get dressed. A lot of dresses lined her closet. Frisk didn’t hate dresses, but wouldn’t mind seeing herself in a suit…like some of dad’s men. She knew dad hated the idea of his remaining child getting into such a dangerous business, but damn it she was twenty years old now. She knew what she was getting into and…maybe she could find out what happened to Asriel. Something, anything, was better than nothing. What else was she gonna do with her life? She couldn’t leave home without someone coming with her, she couldn’t’ go to college without having an entourage around her at all times. Frisk couldn’t stand doing nothing while her brother was out there somewhere missing.

     After looking through her clothes a bit, Frisk picked out a simple blue dress and started to change out of her nightgown. The dress hugged her body just enough to show off her natural curves and enough of her chest to prove that she developed nicely for a young woman. The skirt of her dress ended at her knees and the upper part of her dress just needed to be buttoned. To go with her dress, Frisk slipped on a pair of her black leather pumps before going towards her dresser. Her dresser had a mirror on top of it. On the dresser’s surface she had her brush, a makeup box, and a music box. Frisk looked at herself in the mirror as she started to brush her hair. While Frisk wasn’t the most beautiful woman in the world, she was rather cute and had a lot of charm. Her brown eyes matched her hair and sparkled with life. Her tan skin was soft and barely had any flaws. Her features were soft and rather feminine. It was easy to see why her father didn’t think she was cut out for dangerous work, but despite her gentle and feminine looks, she was a rather tough girl. Her years before that took her in made sure of that. She’s been through a lot at a young age and all the years of comfort hadn’t changed that. She still easily remembered what it was like to get beat and cut. Phantom pains started burning her body and she forced any thought about the past out of her head.

     When she finished brushing her hair, Frisk opened her makeup box and pulled out some lip stick. While Frisk wasn’t a woman fond of makeup, lipstick was an exception. It was easy to put on and done right, it was all she really needed if she was going to put any makeup on in the first place. She loved the dark red color anyway, so she only really put it on for herself. It wasn’t like she was looking for anyone to share her bed with. She had other things plaguing her thoughts at the moment, so romance wasn’t even a thought that crossed her mind these days.

     Just before leaving, Frisk looked at the music box on her dresser and felt her chest tighten a bit. Part of her was tempted to hear the box’s sweet music and look upon what was inside of it, but knew it would only cause her further pain. Before Frisk could be tempted any further, she walked to the door and quickly walked out of her room, closing the door behind her.

 

 

 

     Frisk walked downstairs and went straight for the kitchen knowing her mother would be there making breakfast. She silently hoped her father would be there this morning while she still had courage and determination in her heart. When she walked into the kitchen she was greeted with the sight of her mother cooking pancakes for breakfast. She already cook a big stack, more than either of them could eat and felt a little hope rise up in her chest. The kitchen was rather humble for a mob family to have. In fact, their house in general was rather humble considering what her father did for a living, but her family wasn’t the kind that often liked to flash their money. In a way, it was better this way anyway, because no one suspected such a humble home to hold one of the largest crime bosses in the city. It was a nice house for sure, but nothing over the time and just isolated enough to keep too many unwanted eyes looking into things that might go down in the house itself. Nothing illegal went on in the house, mostly just family meetings, but if people saw a small army of well dressed monsters entering the house then it might raise some eyebrows.

     “Good morning sweetie”, her mother sweetly greeted as she looked up from her cooking for a moment to look at her daughter, “You look really pretty this morning.”

     Frisk chuckled a little. Mom always said she looked really pretty every morning, but it still gave her a little confidence boost to hear it.

     “Good morning mom and thank you. You look really pretty too.” she replied sweetly.

     Toriel chuckled a little before thanking her and turning her attention back to her cooking. It was rare to ever see her mother not looking beautiful. Even in her older age and slight look of tiredness in her eyes, Toriel still managed to be one of the most beautiful women she’s seen. Though seeing that tiredness and sadness in her eyes did make Frisk hurt a little, but it also gave her a little boost of determination she needed to talk to her father.

     Just as she thought about him, she could hear his voice coming from the dining room, also used as the meeting room when Asgore needed to speak about future plans with everyone. Before Frisk was told the truth, Asgore would hold these meetings long after he was sure she was asleep. To this day he still likes to do what he can to make sure she didn’t listen in to his meetings too often, most likely to keep her from hearing the crimes her father was committing

     When she walked into the dining room, she saw someone she didn’t expect to see so early this morning. Sitting at the table across from her father which a cigar in his mouth was Sans the skeleton, one of her father’s most trusted job men. She had gotten close to the skeleton over the last couple of years. While Asgore worked hard to keep his business away from his family most of them time, he had no choice but to make his mob family closer to his personal family after Asriel disappeared. Given Sans was one of his most trusted men, he often had Sans look out over her when she wanted to go somewhere to make sure nothing happened to her. It annoyed her a lot at first to constantly have someone come with you everywhere you went, but after really getting to know the skeleton monster, she found herself enjoying his company. He was wearing his usual outfit of a long white button up shirt with a black waistcoat and a pair of black trousers to go with them. He looked a little tired this morning, but other than that had his usual grin plastered on his skull.

     When the two monster men realized someone had joined them, they stopped what they were talking about and looked at her. Asgore looked more tired than usual. Her father was already an older man when they adopted her, but after Asriel disappeared, he looked even older then he really was. Frisk worried that Asgore was pushing himself too hard, but he was good at hiding just how worn down he really was. Despite how tired and stressed her father looked, some of that stress disappeared when he saw her, even managing to smile proudly at the woman his daughter had become.

     Frisk even noticed Sans’ seemingly permanent smile widened a little when he saw her. He looked tired himself, but not for the same reasons. Even though he was one of her father’s best men, he was also one of the laziest. He didn’t like working too much, but did it out of loyalty, especially if it was important. Sans was mostly interested in napping and telling dumb jokes most of the time. He even told her that his favorite job was basically being her bodyguard since he basically did nothing for a couple hours and just spent time with someone he liked.

     “Good morning sweetie.” Asgore greeted her tiredly, trying to make himself look not as beat up as he did a moment ago, “How are you this morning?”

     “I’m fine…” Frisk answered, but she paused for a moment, hesitating, before opening her mouth again, “Dad…we need to talk.” 

**Notes for the Chapter:**

> I was going to do a little bit more with this chapter, but it was going on so long already that decided to stop it there for now. I wanted to ask you guys though, do you like the length of this chapter to go on for the rest of the fic, a little bit short, or maybe even a little bit longer? I want this fic to be a joy for you guys to read so please let me know what you think so I know just how long or short I should make each chapter!


	3. Of Little Comfort

     This is it; she was finally going to put her foot down. She knew it was going to be an ugly conversation, especially one so early in the morning. Frisk really didn’t want to do this while Sans was here to witness the explosion that might take place between father and daughter, but if she didn’t do this now then it won’t ever happen. It hurt her heart to see such a tired, yet caring expression on her father’s face as he looked at her to give her the attention she had asked for. She needed to do this, not just for herself, but for them too. Yet, despite all the courage she managed to muster up for this moment, no words came from her lips. Frisk tried to force them out, but her voice failed to work. The longer she looked at her father, the more her courage began to falter.

     She couldn’t find it in herself to stir up her father while he was so exhausted. Frisk knew for a fact that voicing her determination to join the business would cause an argument between them. The thought of making her father, who was already suffering emotionally, suffer even further while he was so tired wasn’t something she could bring herself to do. Suddenly, all the courage she had disappeared and she was once again, unable to bring herself to put her foot down. Frisk was getting more and more frustrated with the situation, but she would have to be frustrated for a little bit longer. She didn’t want to push her father any further then he already was being pushed. He was already struggling to handle what he was currently dealing with and Frisk couldn’t bring herself to add another level of stress to his ever growing tower of exhaustion and frustration.

     Her frustration must of started to show on her face because both her father and Sans started to look concerned at her. It also didn’t help that she had been quiet for awhile despite demanding her father’s attention in the middle of a meeting. Neither monster looked bothered by her disturbance at the time, but now that her courage was gone, she felt herself shrink. Suddenly, she started to worry that she interrupted something important now that she was failing to go through with her plan. After all, Asgore rarely asked for Sans to come to his house so early in the morning unless he needed something. 

 

     “Oh…” Frisk somehow managed to speak, trying to find the right words. “I didn’t mean to interrupt. We can talk later Dad, it’s not that important!”

     As she spoke, Frisk could feel her face redden a bit, feeling more embarrassed by the second. She watched her father’s expression change to one that told her that he wasn’t entirely convinced by her words, but accepted it for now. Sans shared the same expression, but seemed a bit more concerned towards her then her father appeared.

     “Well, if you say so dear.” Asgore replied with a unsure tone, but gave her a smile anyway, “We were discussing a couple of small things, but thankfully, nothing too important.”

     He gestured to a empty seat at the table and gave her a more welcoming smile, “Sit with us dear. Your mother should be done making breakfast and making some tea for us soon. I’m sure Sans wouldn’t mind enjoying something to eat before the two of you enjoy your time out.”

     “I could never say no to a free meal.” Sans playfully spoke, becoming more relaxed for now and even making her father smile a little in amusement to lessen the tension in the room.

 

 

     Breakfast was a little more tense than usual. Even though Toriel’s sweet nature and Sans’ laid back and comedic presences were there, Frisk suspected that her father knew exactly what Frisk was wanting to say before backing out of it. Every now and then as they ate and chatted together, she would notice Asgore looking over at her with a bit of concern and worry despite the fact nothing was said recently to cause it. Frisk made it no secret in the past that she wanted to be a part of the crime world her father ran and Asgore was very good when it came to people. It wasn’t hard for him to read her, so it wouldn’t be a surprise to her if he had already figured out what she wanted to talk about. Still, there was still an intensity in the air between them, but Toriel and Sans presence made it a little easier to ignore until everyone had their fill.

     Sans got up from the table with a grunt, putting a hand on his non-existent stomach and spoke up with a pleased grin, “I appreciate generosity Boss and Mrs. Dreemurr, but me and the little lady should probably hit the road soon.”

     Frisk was a little thankful for Sans bringing up that Frisk and him needed to get going soon, giving her an excuse to escape the intensity between Asgore and her. The sooner she got out of the house, the better she would feel.

     “Ah, I suppose you’re right.” Asgore responded as he stood up from his chair, “Don’t forget to visit those businesses we discussed while you’re out, just make sure everything is well.”

     Sans gave him a nod as Frisk got up and started to make her way out of the dining room before she heard her father’s powerful voice call to her. “Frisk…”, he called, waiting until she turned to look at him before continuing, “Forgetting something?”

     Frisk’s felt her face get a little red, but smiled as her father opened his arms to give her a hug. It had become a tradition that Asgore hugged her before she left the house. It was an unspoken thing that Asgore showed his wife and daughter affection often. Everyone was aware that because of the business, there was always a good chance something could happen to them at any moment. It was one of the reasons why Asgore didn’t like his wife and daughter leaving the house without someone in the business coming with them, especially after what happened to Asriel.

     She walked back to her father and gave him one of her famous hugs. A warm smile grew on her face as she felt her father’s massive arms wrap around her small body. However, he hugged her noticeably tighter then he usually did, only confirming to her that he knew exactly what she wanted to talk about. He was scared and she didn’t blame him, but this was something she needed to do, for all of them. Regardless, a word about it wouldn’t be spoken between them until he came back home later tonight.

     As Frisk felt her mother kiss her forehead, Sans walked to the front door and grabbed a black trilby hanging on a hook near the front door, completing his outfit. After completing her near daily ritual, Frisk finally made her way to the front door to join Sans.

     He jokingly opened the front door with a cheeky grin and bowed to her once her parents were out of eyesight of them, “After you little lady.”

     Frisk rolled her eyes, but smiled with a little chuckle regardless as she stepped out the door, feeling the weight on her chest get just a little less heavy, for now at least.

 

 

     “You wanna tell me what that was about?” Sans asked with a bit more of a serious tone then he usually had after walking with her in silence for a few minutes.

     “What do you mean?” Frisk asked a bit nervously, pretending not to know what he was talking about.

     “Frisk…” he sighed, stopping in his tracks before looking at her. Seeing that he stopped walking, Frisk stopped as well, meeting his eyes.

     While Frisk wasn’t a very tall girl, Sans wasn’t a tall monster either. When she was only a couple of inches taller than the monster, but he knew how to make her feel so much smaller. His eyes looked at her’s seriously, knowing full well something wasn’t right with her. They spent enough time together for Sans to know when she was just pretending to be okay and unlike her father, he didn’t accept her word. He knew full well that Frisk wouldn’t say a word to someone if something was bothering her out of fear of burdening another person and he knew that was exactly what she was doing now.

     “Sans…” Frisk sighed in frustration, moving her arms to hold herself tightly, something she often did when she was uncomfortable, “You know what’s wrong.”

     Sans looked at her quietly for a moment and shook his head a little. “You know Asgore’s not going to let you in. No amount of talking will change that.”

     She looked at the skeleton with a bit of sadness in her eyes, “I know that…” she responded softly, “But I can’t just sit around while my brother might be out there somewhere.”

     A bit of sympathy grew on Sans’ face, “Frisk we’ve been over this. If someone took him, we’ve would of gotten a ransom note or something by now.”

     A flash of anger rose in her at his response, quickly snapping back, “And if he was dead we’ve would have found his body by now!”

     His eyes widened a bit out of surprise. Frisk has never snapped like that at someone before, even she was a bit surprised by her response and immediately regretted lashing out at him. She held herself tighter and looked away from him for a moment as she tried to compose herself.

     After being quiet for a moment, Frisk softly spoke up again with pain in her voice. “Something’s up Sans, I know it.”

     Frisk looked at Sans with a pained expression, “If another mob was involved they would of used him to scare us. He would have been found relatively easily…yes…there was no ransom note…but there was no body either…”

     She paused for a moment, her eyes starting to grow wet and when she spoke again, her voice was shaking. “Sans…I just want to know if my brother is dead or not. That's all...I just want to know if I should be hopeful...or if I need to begin mourning him...it's eating us alive and I just want us to finally be able to move on.”

     Frisk was fighting the urge to cry when she felt a pair of arms wrap around her, hugging her tightly from behind. She could feel his soul pulsing through his chest against her back. He was quiet for a moment, just letting her body slowly steady itself and relax in his warm embrace.

     “I get it…” She heard Sans respond as he tightened his hug on her, “He just doesn’t want something to happen to you by putting yourself in danger…none us do…it would kill us if something were to happen to you too.”

     Neither of them spoke for a moment before Sans let go of her and turned her around so he could look at her in the eyes.

     “Look…we’ll find something…eventually and when we do, you’ll be the first person to know. Now come on, let’s try to make this a good day dollface.”

     Sans gave her a smile, using a nickname he recently started to call her by to try to get a smile on her face too. While she did manage to relax a bit and get a little smile on her face, she found little comfort in his words. She knew Sans was trying his best to make her feel better, but there was only so much he could do. Still, while she appreciated the effort, she doubted anything could make today into a good day. Though, being with Sans did help made things just a little less shitty.


	4. Silence

     Frisk didn’t talk much after Sans attempted to comfort her. While being with him did put her more at ease, she realized that there truly was no one she could really talk to. Sans was just like her father and didn't want her to have anything to do with the business they were involved in. He made his feelings towards the idea well known to her in the past, but in a way, hoped he might be swayed if she explained herself a bit more then she had in the past. In the end though, it just made things awkward between them. If there was anyone she knew that might understand where she was coming from, it would have been him. Sans had a brother of his own, one he cared about intensely, so she expected for him to have…more to say or something more comforting then what he ended up giving her. Sans was normally so good at saying the right things and making her feel better when she was down, but this time, when she really needed it, she barely felt much better after talking to him. Maybe Sans realized this and knew there wasn't much he could say to her now that would make her feel better because after their short talk, he didn't speak much after it either. For once, Frisk felt strange around him and didn't know how to make it better. 

     It was a short walk from the house until they reached a drive way that was a bit of a distance away from the house. The driveway was designed to be a good walk away from the house intentionally. With so many trees surrounding the house, it was nearly impossible to tell that there was even a house there in the first place, so if anyone who wasn’t involved in the family business came down this way, it was often safely assumed that the road just lead to a nice view of the wilderness, but not much else. Every now and then a random driver would use their drive way out of curiosity of where it lead, but often ended up leaving rather quickly when they realized it just stopped with no real destination in plain sight. Sans checked the time with the watch on his wrist, seeing how long the duo would have to wait before their ride would arrive.

     As per usual, Asgore called a ride for his daughter and his job man whenever they went out. Despite Sans having the full ability to teleport wherever he wanted to go, he rarely used it while he was with her. He told her that it was because while he had plenty of magic, it was limited and Asgore wanted him to save it for when they really needed it since Sans was often drained of his magic rather quickly, especially in intense situations. Neither of them mind the ride though since it often just gave them more time together, but today Frisk dreaded how quiet the ride was going to be. While it was a bit of a drive for the driver to get to her house, it was rarely a couple of minutes worth of waiting. Normally the wait felt like nothing since Sans typically would make the time blaze by with their talks and ways of making her laugh. Today though, the wait felt unusually long due to the silence between them. Frisk looked at Sans out of the corner of her eye and saw for a moment he was looking at her before quickly looking ahead of himself when her eyes landed on him. For a brief moment, Frisk thought he looked…worried, maybe even scared before he looked away. She began to feel the weight in her chest get heavier, pressing down hard against her soul. She hated this, hated being quiet like this with a guy she cared about whom rarely knew how to shut up.

     Suddenly Sans cleared his throat and caught her attention again. For a moment, she expected the sound to be his way of grabbing her attention to start talking again or making a random joke, but nothing came from the usually chatty skeleton. She started to feel more and more uncomfortable. Now that she looked at him, she could see his face was a bit more serious, the light in his sockets were dimmer than usual. He looked like he was deep in thought rather than upset. Maybe the sound was an attempt to break the silence between them, but he wasn’t sure how to make things better. Frisk didn’t know what could be rattling around in the skeleton’s head, but it started to make her concerned seeing him so serious.

     Just as Frisk opened her mouth to try to say something, a black car started to come down the driveway. Suddenly, the look of deep thought disappeared off his face and Sans seemed to get visibly less tense. She realized in that moment that his body was more stiff in that moment then she’s ever seen and the sight of the car made him loosen up to what she was use to. When the car drove up to them, Sans walked to the car and opened the back passenger door for her as he usually did, this time having a forced smile on his face. Frisk gave him one of her own as she sat down and waited for Sans to shut her door before letting a sigh out, louder then she meant to.

 

     “Tra la la la. Things are not what they should be.” A voice from the front driver’s seat sang out.

     The driver of the car was the only monster she’s ever seen driving any of the cars she’s been in. While she never saw the monster’s face thanks to his grim reaper styled cloak, that kept their face and body completely hidden. Frisk wasn’t even sure if her driver had any specific gender for they rarely talk about themselves and their voice gave no real clues to what their sex might be. Despite all this, the driver was very skilled at what they did and often was very observant of their surroundings. While they didn’t talk often, when they did it was often advice about what was discussed or pointing out something their passengers may or may not even be aware of. Just hearing her sigh might have been enough for them to know something wasn’t right.

     Before Frisk could say anything to them though, Sans opened the door to the other side and sat down beside her, still acting unusually quiet around her. Neither of them needed to tell the driver where they wanted to go since they rarely ever went anywhere outside of the city. So once Sans took his seat, the driver was already driving them back the way they came.

     The drive was just as awkward as the wait for it was. Frisk mostly looked outside her tinted window with everything and nothing running through her head. After a few long minutes of silence, Frisk looked over to him and saw that Sans was doing the same thing she had been doing for almost the entire ride. Sans stared outside the window, his eyes looking a million miles away as he held his chin in his hand.

     Frisk suddenly found she could not stand the silence between them anymore. She hated every silent moment that passed. Sans told her they should try to enjoy the day and so far, neither of them were and she felt that this silence had gone on long enough.

     She turned her body a little more towards him and opened her mouth, her voice barely making it out of her throat, “You know…if the mafia business doesn’t work out for you…you could always join a band.”

     Sans, who seemingly got knocked out of his trance from the sound of her voice, looked over at her with a bit of a confused look on his face, “What was that?”

     “I said…” Frisk spoke with a bit more of a cheerful voice and a real little smile on her face, “If the mafia business doesn’t work out, you could always join a band.”

     A little chuckle left him as he smiled a little more naturally and asked, “What makes you say that?”

    “Because I heard you’re really good at playing the sax-a-bone.” She finished with a bit of a grin on her face.

     Sans was quiet for a moment before letting out a little laugh and the light in his eyes grew a little bit brighter. A bit of warmth grew in her chest and felt it get just a little less tight seeing him smile and laugh again after such a long and uncomfortable silence between them.

 

     That one dumb joke was enough to break the tension between them. The rest of the ride to the city was filled with laughs and terrible puns. That was something she always loved about Sans, he had a sense of humor that’s unlike anyone she’s ever met before. It was simple, but he always laughed at his own jokes or seeing people’s reaction to them, even if it was a look of disappointment or even a glare for making such a dumb joke. It was a sense of humor that Frisk rarely got to share with someone sense she had a soft spot for really dumb puns herself, but Sans was the only person who was more than willing to entertain her with his endless supply of puns.

     Suddenly, time flew by so quickly that when the car finally stopped at their usual drop off area, Frisk was surprised that the ride was done so quickly. She thanked their mysterious driver who gave nod so light that she struggled to see if he even reacted at all, but he rarely reacted to anything beyond simple conversation.

     She opened the door and stepped out onto the sidewalk, seeing some people walking the street looking at her as they passed by her. It wasn’t that odd to see people staring at her, mostly because not long before she exited the car, there would be a well dressed monster by her side. Monsters were becoming more of a sight in the human world now that the monster mafia was taking up more territories in the city, but it didn’t mean a lot of humans were happy about it. Humans could barely find themselves comfortable around their own kind just based on their skin colors. How could humans be comfortable around people that look absolutely nothing like them?

     That was one of Asgore’s goals, to make a place for monsters and humans. While naturally people got hurt in the progress and was involved in illegal business, the monster mafia was far more understanding towards the innocent then human mafias were. Protection fees were a lot more reasonable and if innocent people couldn’t pay on time, they would get an extra two weeks to come up with the money. Their protection fees were mostly given to businesses rather than people just trying to survive. Businesses had more breathing room most of the time, but even the bigger places got time extensions if need be.

     However, if the business had shady owners or owners who tended to abuse this generosity, people like Sans would give them a visit with rather…unpleasant intentions. No extensions were given to these people for they have more than enough to pay their small fees and those who try to abuse it, will get to see what happens when they try to screw over the monster mafia. Asgore and his people were patient and kind people for the kind of business they were involved in, but he was not the kind of man to cross either and sometimes, people needed to be reminded of that. 

     Once Sans joined her side, he reached into his suit and pulled out another cigar, the previous one he got rid of before eating breakfast, and placed it between his teeth. For the moment he opened his mouth, Frisk got to see the pair of sharp fangs that were normally impossible to see with his grin. Every time he opened his mouth there was always a set of fangs that could been seen, but it often baffled her how she saw them so often, but never saw them in his grin. It one of the many mysteries of monsters she supposed. With the cigar placed between his teeth, Sans lifted his thumb and summoned a little flame from it, taking a moment to light his cigar with a satisfied grin on his face. 

 

     “I’ve been thinking…” He spoke up in an unexpected way after taking a puff of his cigar and pulled it out of his mouth to hold in his hand, “about what you said earlier. How you wanted to join the family just so you can try to find out about your brother…”

     Sans paused for a moment, looking at Frisk out of the corner of his eye. Frisk didn’t say anything, but looked at him with a bit of surprise and curiosity. Was he seriously reconsidering talking to her dad?

     “I honestly think this business will be too rough on someone like you…” he confessed, the light in his eyes dimming a bit as a saddened expression took over his face.

     He looked at her directly now as he spoke to her, “You’re kind and sweet…to everyone, even strangers…I don’t want this world to change you into something you’re not…and…it will change you.”

     He paused again before finally allowing another small smile to take up his face, but the light in his eyes remained dim, “But…like you said…you’re 20 now. You’re gonna do what you want regardless of what everyone else wants…so…I was thinking…”

     Sans paused one last time, this time however when he spoke, he sounded dark, almost sinister. The change in his voice was enough to make a chill run down her spine as his eyes almost went completely dark, but his grin grew a little more. A voice and expression she’s never seen from him before and it nearly frightened her.

     The words that left his mouth only added to that as he practically whispered, “How about a taste of what you would be getting yourself into?”


	5. AUTHOR'S UPDATE

     Hey everyone! Sorry that this isn't a new chapter per say, but I felt I really needed to update everyone since it's been so long since this has been updated. I've been going through a lot lately and had no time or energy to write, even for my book. My fiance and I had a really bad scare with a family member and we've been struggling a bit financially so I'm having to work more to make up for it. I haven't been able to actually sleep and along with stress it's been extremely overwhelming and left me drained and unable to write as much as I want to. I'm not discontinuing this series or anything like that, I just feel like I needed to say something on why it's been taking so long for the next chapter to come out. Once things clear up and I finally have time and energy to write, things should get back to normal and I'll be able to update more. Thank you to everyone for the kudos and nice words! It really helps and I love and appreciate you all! 


	6. Collection

**Notes for the Chapter:**

> After finally getting some time to write, I'm excited to present the next chapter of this fic! I made it longer than I usually would to make up for the wait and as a test to see if you guys would like longer chapters! I also want to point out, after doing some thinking, I decided to make the monsters of this world bigger than I originally had them so Sans is now Bara Sans for reference. It's not a major size difference, but he is much bigger than her. Hope the change isn't too distracting or out of nowhere! Anyways, enjoy!

     Sans’ words sent chills down her spine. The way he basically whispered them in an almost menacing tone she never heard from him before was enough to make her question what she had asked for. As they walked side by side to a place unknown to her, Frisk couldn’t help but wonder what the skeleton monster had in mind. Her father never went into detail what exactly the monster mafia did besides reasonable protection fees. It wasn’t hidden from her that sometimes they had to hurt people, sometimes even kill them, but they never went into detail about that. Frisk realized that she knew so little about what she was asking to join. Maybe it wasn’t such a bad thing that Asgore and Sans didn’t want her joining yet, especially since she was so ignorant about what their business actually did or how they did it. Suddenly, Frisk’s confidence in her decision started to wane.

     As they walked side by side, Frisk glanced over at Sans seeing him enjoying his cigar with a unusually wide grin on his face. There was something unsettling about that grin like he was planning something and that was unsettling. Sans was quite the prankster so just the idea that he was plotting something made her a little on edge. His pranks were never cruel or overly mean, but in this case, things might be different. He might try to scare her into changing her mind, but she had to be stubborn. Even though she’s ignorant about the business, getting involved might be her best shot to find out what happened to her brother, even if she had to do bad things. After all these years, no one could find anything leading to what happened to him, maybe she could change that.

     It seemed like hours before they made their first stop at a nice looking hotel right in the middle of some of the most popular stores in the city. Sans took one last puff of his cigar before taking the end of it out of his mouth to toss it aside onto the street. Smoke from the cigar slowly escaped his mouth, giving him a more menacing look as the light in his eye sockets was swallowed up by the darkness. In just a few seconds, Frisk witnessed Sans seemingly switching personalities from the one she knew to one she’s never seen before.

     “Stay by me. These folks shouldn’t cause us much trouble, but there are some…undesirables…” Sans warned her, the tone in voice seeming more sinister than she’s ever heard it before.

     Frisk almost didn’t recognize the skeleton monster beside her now. This wasn’t the fun loving, goofball she knew anymore. This was a monster that was willing to get his hands dirty if things didn’t go his way. Sans was already pretty intimidating due to his size alone, but seeing him so serious was enough to send chills down her spine. He started to make his way up the short set of, waking Frisk up from her thoughts and quickly following after him.

     Once they reached the heavy set of dark doors with golden handles, Sans reached forward with a large hand and opened them with little effort. He gave a little nod towards her, giving her a silent offer of letting her go in first. Even as this version of himself, Sans was still a gentleman to his female company and Frisk couldn’t keep herself from smiling a little as she took the offer of going inside first.

     The inside of the hotel didn’t seem anything more like a nice place to stay. It was clean, well organized, very professional, and seemingly on the higher end of class and price. Nothing gave away that anything shady was happening within these walls, but they had to be here for a reason. Her father didn’t have an interest doing business here if there wasn’t something to gain from it. It could just be a simple protection fee collection from a business that wasn’t hurting for money, but with everyone she saw, both employee and guest, looked like honest people. Sans had warned her of undesirable company being around them, but there wasn’t anyone who looked dangerous to her here. However, there was still plenty she didn’t know yet.

     Sans followed her inside, passing by her and heading towards the front desk where a young man stood dressed nicely in uniform. When Frisk caught up with Sans, she noticed the young man had a strange look on his face, like he was frightened of the monster before him, but tried to hide it from plain sight and doing so poorly.

     “How can I help you sir?” The young man asked with a bit of a nervous voice.

     “I’m here to see Mr. Coleman. We have an appointment…” Sans answered with a more menacing emphasis on the last word.

     “Oh yes…” He replied a bit more nervously, his attempt to hide his fear becoming weaker by the second. “He’s up on the VIP floor, waiting for you.”

     “Perfect.” The skeleton monster grinned widely, “I shouldn’t keep him waiting then.”

     Sans made sure Frisk was beside him as he made his way to the elevator. He pressed the button to summon it to the ground floor and he adjusted his outfit as they waited for it. Frisk felt tense around him again. This Sans wasn’t nearly as talkative, let alone easy to talk to. While most of the time their silences weren’t uncomfortable, this one was almost more uncomfortable then the one they said in the car before they started the pun war. He looked at her through the corner of his eye and smiled to himself about something, but before she could ask, the door to the elevator opened. The elevator operator was smiling for a moment, but once he saw the massive monster beside her, his smile became more forced as the color drained from his face.

     The two of them stepped inside and the operator kept his eyes on the buttons as he asked, “What floor would you like?”

     “The VIP floor, if you please.” Sans answered as he pulled another cigar from his coat.

     The operator seemed to already know the answer before Sans even answered as his finger was over a button before he even opened his mouth, but now with confirmation, he finally pushed it. Sans placed the cigar in his mouth as they began to move, but hadn’t light it yet, perhaps waiting until they were in a less confined space so Frisk wouldn’t be trapped in a small elevator full of smoke. The silence between the three of them was tense, but as they arrived to the floor, Sans finally spoke up.

     “Watch and learn sweetheart.” He grinned without looking directly at her, seemingly smug about what he was about to do.

     Once they finally arrived, Frisk was bombarded with sights and sounds that she hadn’t seen before. The entire VIP floor was full of music and laughter as men with cigars and cigarettes played at card and roulette tables. Some men were spending time at the bar with pretty women around their arms, wearing dresses that showed off more scandalous parts of them without revealing everything, yet at least. Frisk immediately realized what kind of place Sans had brought her to, a gambling den with plenty of female company with plenty of rooms to enjoy them in. Now she understood why Sans wanted her close. These men could eat her alive.

     Sans stepped out of the elevator, immediately grabbing the attention from many people in the room, if not everyone there. However, he wasn’t the only one getting eyed. Some men were more interested in the company he brought with him. While some seemed to tense at the sight of the monsters, there were others that were looking at Frisk with a look that made her nervous. Suddenly, her modest dress felt too revealing and her hands held onto each other around her thighs, as if making sure the skirt of her dress didn’t rise up more unintentionally. She wasn’t the only one that noticed either. Sans gave some warning glances as he passed by. She even noticed his hands balling up, seemingly ready to punch anyone who got too close to them.

     Frisk followed Sans blindly, becoming more aware of the strangers around her than him, suddenly finding herself at the bar. Sans had already found the man they were looking for, like he knew exactly where he would be. She saw him face to face with a older man with a cigar in his mouth and a pretty woman sitting in his lap with her arms around his neck, giggling as he whispered into her ear. However, the sight of Sans was enough for him to push the woman off rudely and turn his attention to the monster with a confident gleam in his eyes.

     “Ah, Sans! Good to see you!” The older man greeted warmly with open arms. His attention turned to Frisk and an almost predatory grin grew on his face. He reached out a hand to her in a gentleman fashion. “And who is this pretty thing? A new…young lady Asgore sent to us for giving lonely, rich men company? I was expecting a monster to expand the options, but who am I to turn away pretty help?”

     Frisk almost let her hand touch the man’s for the sake of being polite, but Sans stopped her, his eye sparking with hints of a blue flame within it. “No, she’s not one for you or your clients to touch. She’s with me.”

     The man’s smile only widened with slyness to it, “Ah, finally found someone to enjoy these days? She is a pretty thing, but so small too…makes me wonder how-“

     His words were cut off by Sans’ hand as he grabbed his suit by the chest and lifted him up off his stool, not high enough to lift him completely in the air, but enough to get his point across. “What she is to me isn’t your business. I’m here for the money, Mr. Coleman.”

     Mr. Coleman’s confidence dwindled into nervousness as he awkwardly chuckled as Sans held him in the air, “Ah, didn’t mean offence, I got your money. No need to worry about that.”

     “Good.” Sans said blankly as he lowered the man down to his seat once more. “I didn’t want to make a mess in your nice establishment, especially among your friends.”

     “Yes, yes, of course.”Mr. Coleman chuckled nervously as he reached into his coat to pull out an envelope stuffed with money. “I wouldn’t try to mess with your people. I learned from the past.”

     “Pleasure doing business with you Mr. Coleman.” Sans replied more causally as he finally let go of the man and taking the envelope to hide away in his own coat. “If we find you’re just one cent short, we’ll be back and it won’t be so pleasant.”

     “I assure you everything is there and it’s been a pleasure.” Mr. Coleman replied, only giving Frisk a look and saying with a kind tone, “And have a lovely day young lady.”

     Before Frisk could say anything, Sans put a protective arm around her and guided her with him out and back into the elevator. Once the doors were shut, Sans seemed to become less tense, “That was a easy one. Mr. Coleman doesn’t try to fuck us after the first time when he didn’t take us seriously. He knows better now…” Sans paused for a moment and looked down at her, “Are you okay?”

     Frisk was quiet for a moment before looking up at him with a smile, “I’m fine. Just…wasn’t expected to get looked at that intensely.” She chuckled a little nervously, glad she was finally out of sight from men trying to undress her with their eyes.

     “I’m not surprised. You’re a very pretty young lady. You get looked at more than you think. It’s just not as obvious.” He answered matter-of-factly as he examined his cigar in his hand before putting it back in his mouth, still keeping it unlit but seemingly just wanting to have one in his mouth.

     His words surprised her a bit, not expecting such a nice and flattering compliment from the big goofball. She felt her cheeks blush a little and smiled a bit warmly, “Wow…wasn’t expecting that, but…thanks.”

     Sans gave her a little smile and a nod as their elevator reached the bottom floor. Once the doors opened to the main lobby, he finally lit his cigar, taking in a puff and letting the smoke escape his mouth. “There’s just one last place to check and then we can do what you wanted to come here for. This next one though…isn’t gonna be as easy as Mr. Coleman was.”

   

 

 

 

     The next stop wasn’t quite like the hotel, but a place that is frequently visited when the sun went down. It was a pretty popular jazz club that Frisk had heard her father attending to from time to time when he had to do business with the human mafia or certain clients, but she’s never been inside herself until now.

     Before they went inside, Frisk asked curiously, “Is this another collection?”

     Sans put on his serious act again, but answered her nonetheless, “Yes. Most collections will be pretty easy. We got most of our people to understand not to fuck us, but this guy…hasn’t learned that yet. This is his third time coming up short and that’s when we start to get physical. I won’t be too rough on him this time since this is your first time, but it will get…graphic.” There was a slight glimmer of sadness in his eyes when he finished, looking a bit scared as he met her eyes.

     Frisk immediately knew why though. She was scared seeing him violent would sour her image of him and potentially scare her to see the man he has to be for this line of work. While the idea of seeing Sans hurt someone sounded upsetting and scary, she had to see it because one day, she might be the one that has to get her hands dirty herself. She gently touched his hand with a soft smile and reassured him, “Hey, whatever you do in there, I know it’s not you. Just someone you have to be…someone I’d have to be…you do what you have to do…I won’t judge you…”

     Sans seemed to lighten up at her words as he smiled at her more confidently and gave her a nod. “Alright…be strong though…this is gonna get messy…”

     The inside of the club was pretty much what Frisk expected. The walls and floor were purple with all the lights on, but she could imagine the lights when the club was actually open would alter it to a darker, more soothing purple, if not almost black. There were tables and chairs everywhere with a bar in the back and a stage in front of everything for the performers to sing and play on. A few neon signs and paintings decorated the walls, but nothing too distracting from the main entertainment. It looked like a nice club, but a typical club nonetheless.

     Near the center of the club cleaning off a table, there was a slightly disheveled man dressed in a slightly messy suit whose eyes met Sans’ seconds after he walked in. The man’s eyes narrowed and his mood looked even more soured then before. “Hello monster…” He grumbled. “Come to leech off me again?”

     Sans’ usual grin turned into a more cruel one. “Of course…you still owe us…a lot.” He spoke, slowly making his way towards the man. Before Frisk could follow him much more, he made a gesture with his hand to stay where she was, assumingly to keep her out of danger. “You’ve come up short on us three times now Earl…I warned you the last time…if you fucked us again…you were gonna have a bad time…” His eyes grew more sinister as a small blue flame burned in his left eye as smoke from his cigar escaped his mouth, nose, and eyes, giving him a more demonic look than before.

     “You think I’m scared of you monsters? Think you’re so tough?!” The man started to yell, throwing the rag he used to wipe off the table onto the floor and starting walking towards the skeleton monster with rage in his eyes. “You ain’t shit! Asgore’s too much of a flower loving pussy to do any-“

     Earl stopped in his place, completely freezing in place as Sans barely lifted a hand. “Earl…Earl, Earl…there’s a lady present…and you shouldn’t be talking so badly of Asgore. He’s been pretty patient with you…but now…not so much.”

     With a flick of his hand, Sans sent the man flying into a table, knocking him into chairs and toppling the table over with a loud bang. Frisk jumped a little at the sudden lazy throw sending a grown man flying, but kept watching intensely. As Sans walked over to Earl as he tried to get up, groaning and wincing in pain. She could see the slightest sign of blood on the edge of the table. Without giving him much time to recover, Sans grabbed the man with his magic again, throwing him into the bar before teleporting and slamming his head into the bar’s surface, breaking a glass with his face. The man screamed in pain as shards of glass dug into his face.

     “Motherfucker!” the man shouted in pain, “You fucking freak! Ahhhh! What the fuck is this!?”

     “Just a taste of what Asgore wants to do to you. I’m the lazy one…imagine someone more active coming around…” Sans taunted, “Hell, at the rate…you just might find out…”

     “Okay okay!” Earl submitted, “I’ll get you your damn money!”

     “Oh you’re gonna do more than that. You’re gonna pay us what you owe on top of doubling your monthly payments.” Sans grinned, pushing the man’s face harder into the bar before tossing him aside onto the floor.

     “Fuck that’ll ruin me! Are you crazy!?” Earl yelled, holding the side of his bloody face full of glass shards.

     Sans put his foot down on the man’s chest and blew a cloud of smoke into his face, “Should of thought of that before you tried to fuck us. Maybe if you’re good and Asgore feels generous, he’ll lower it back down, but for now, you’re gonna pay us what we want and if you don’t, someone worse than me will come here and you may not be alive after their visit.” He pushed the air out of the man’s chest with his foot before finally letting him go. “Money, in full, or you’re dead, got it?”

     “Okay okay! Just go please!” Earl begged, looking pathetic compared to how he came off before Sans got physical with him.

     Sans left the man on the ground coming to Frisk and guiding her to swiftly leave, trying his best not to look at her directly after seeing her wide eyed. Frisk was still in shock to what she had witnessed. She never saw Sans be so cruel to anyone before and even though she thought she was ready, she wasn’t prepared for what he would do. She was expecting a beating, but nothing that bad and it still had her shaking a bit.

     The skeleton must of saw how Frisk was shaking a little from what she had witnessed and immediately softened up, looking a bit sorrowful as he asked, “Are you okay?”

     Frisk was quiet for a minute before opening her mouth, “I…I think I want to go home…”


	7. Walk in the Park

Frisk didn’t know what she was expecting when Sans wanted to introduce her to the world she was practically begging to join. She knew their family did bad things. She knew that they hurt people, even kill them, but she could never actually see them doing it. These were people who were the nicest people she’s ever met. Yet, she’s never actually seen them work either. Sure, she’s seen her father work, but mostly with calls and meetings with his people. Though, Asgore left the house from long periods of time and there was no telling what kind of things he was doing while he was gone. Seeing Sans brutally beat a man was her wake up call. The screams and the blood haunted her. That dark look in Sans' eye sent chills down her spine. He was so ready to hurt him, ready to do worse than what she saw, but probably restrained himself in front of her. Who knew what he would of done if she wasn't here. She couldn’t be a part of the business if she wasn’t willing to hurt others and she wasn’t sure if she could. She's never hurt anything that wasn't bigger than a trespassing bug. How the hell was she going to hurt someone the way Sans could? She was small, weak...sensitive. How the hell can she do what Sans does on the daily? Now her doubt was growing to the point that Frisk wasn’t sure if she would ever find her brother again.

A voice calling her name broke her thoughts. She was so lost in her shock and doubt that she became deaf to the voice of her skeleton friend. “Huh? Sorry did you say something?” Frisk asked with a little bit of a lost look in her gaze as her eyes met his.

“Yeah…I asked if you were sure if you wanted to go home so soon…” Sans answered with a hint of sadness in his voice and worry in his eye sockets. He lifted a big hand up to rub the back of his skull, uncomfortably.

She sighed softly, quiet for a moment before replying, “I…I don’t know…I just…want to get away from here…” Frisk struggled to find the words as she struggled with herself.

She really wasn’t ready to go home. Frisk would spend days home at a time and didn’t get to go out a lot, so the idea of going home so soon wasn’t ideal, but she wasn’t sure what else to do. It wasn’t like she hated her home or her family. She just didn’t want to be home all day with little to nothing to do for the rest of the day when she could be out doing something in the world, maybe even find something that can tell her what happened to her brother, even if it was very unlikely.

Sans sighed softly and, as if he knew what she was thinking, opened his mouth to say, “We can go to the park, it’s not far from here.”

“Yeah, that sounds nice.” Frisk answered softly, giving her friend a forced smile despite the troubled look in her eyes.

The two of them walked side by side in silence. Sans stuffed his hands in the pockets of his pants with a cigar burning between his teeth. He seemed lost in thought with a stare in his eye that made him look a million miles away. Frisk held herself, attempting to make sense of her own thoughts, but the mental exhaustion was almost too great for her to handle.

Luckily, it wasn’t a long walk to the park so Frisk wouldn’t be forced to be trapped in her mind for much longer. There was something about the park that brought her comfort. Rather it is the sound of leaves rustling in the wind mixing with sound of children’s laughter or the beauty of nature, it always helped Frisk to relax when she was stressed or had too much on her mind.

The two of them were still silent but a genuine little smile did make its way on her lips once they reached the park. Their steps followed the concrete walkway that circled the entire park. Her eyes wondered over to the playground to see human children playing and even a few monster children playing beside them. However, her smile faded as she saw that one of the human children’s mother turn away from another woman she was chatting with and an angered look washed over her face. She got up and stormed over to her child who was playing with monster child and grabbed her child roughly by the arm. Frisk saw her furiously talking to her child before pointing at the monster child and pulling them away from their new nonhuman friend. A bitter taste was left in Frisk’s mouth watching the mother storm off with her child’s arm in her hand, assumingly leaving as she kept walking, leaving the woman she was talking to behind who seemed confused by her actions. The small monster child looked hurt and confused, standing alone now with other human children seemingly keeping their distance from him.

“She wasn’t the only one who noticed the scene. When she turned to look at him, Sans was staring at the remaining child with a dark look in his eye sockets before turning his attention back to the ground. He pulled his cigar from his mouth, letting the smoke flow from his mouth.

“Cruelty towards monsters wasn’t new. Monsters have been nothing but kind and welcoming, but humans lash out at things they don’t understand, even at their own kind. Frisk began to think about the man at the club again. His anger towards seeing a monster was intense. Granted he could be just as rude to humans, but there was just nothing but anger towards the skeleton that stood before him. He even insulted her father. She didn’t know him, didn’t know why seeing him get hurt had hurt her. He insulted her family and yet, she still felt sympathy for him. Asgore and Sans were right, she wasn’t strong enough to handle this line of work. That doesn’t mean she can’t become strong enough though.

“All she’s ever seen from humans was anger and cruelty, rarely were they kind to anyone. Monsters helped her, they cared for her. All humans did was hurt. Why should she felt bad about the ones that deserve getting hurt? She shouldn’t, but she does. She had to change that. Frisk couldn’t let her sensitiveness get to her. Not if she wanted a chance to find Asriel.

With her finding courage in herself again, she looked to Sans again and started to speak, “I’m sorry for being so quiet…I had to process some things.”

“I get it.” He spoke quietly, “It’s…not a pleasant sight, but something you have to see. I don’t want you to come in being blindsided by some of the things you’ll end up seeing…or doing.”

“I know…” She paused for a second before giving him a smile, “Thanks for looking out for me.”

Sans returned the smile and chuckled a little, “We all are…”

There was a bit more silence between them, but it was Sans who broke it again. “So…you still wanna join?” The smile he gave her implied he knew the answer already, but wanted to hear her say it with her own lips.

“Yeah…I’ll have to adjust to some things, but I can handle it. I’m a tough girl, I can handle it.” She replied with a bit of humor to her answer.

Sans chuckled softly before replying, “I hope so at least. So…does this mean you don’t think I’m a horrible monster?”

Frisk laughed a little and answered, “Not at all, you’re just a big, pun telling, skele-TON of fun.”

That got a good laugh out of the skeleton monster as they walked side by side. It was nice finding a way to laugh after what she’s been through today and it gave her hope. If she could find a way to smile after meeting a sleaze bag and watching a man get brutally beaten up, then that was enough to tell Frisk she can do this. She was one step closer to finding her brother.

 

 

**_______________________________________________________**

 

 

Down in the more unfortunate part of the city, a man ran for dear life, running down nearly deserted and cracked sidewalk. He panted hard, his worn down clothes torn with claw marks, blood running down his face from a gash on the side of his head. He tripped over his own feet, falling to the ground and scrapping his knees and arms as he tried to cushion his fall.

“FUCK!” he cried out in a flurry of pain and panic. The man looked behind himself, seeing the figures he was running from taking their time chasing him, the sound of a wooden bat dragging against the cracked and ruined sidewalk. Panicking, he looked around and spotted an alley way between two abandoned buildings. He could see it ended with a chain link fence, but if he was fast enough he could lose them. He couldn’t keep running like this, there was no way to lose them. This risk was his only hope.

Getting up as quickly as he could, the man ran towards the dark alley way. He ran until his hands could grab a hold of the fence and quickly started to climb the fence. About half way up, he looked behind himself to see the figures slowly walking into the alley. There was two, one of them lifting up the bat they had dragging the whole way to lift up to their shoulder. He panicked, working even harder to make it over the fence, but just as he reached the top, a sharp pain shot into his back. A blade dug itself deep into his back, blood running down his back and soaking the remains of his shirt. He let out a silent gasp the second the blade sunk into his flesh. His hands gripped onto the fence even tighter for a moment before loosening up and making him fall hard on the concrete ground. He trembled, frozen in pain and fear as he watched the figures finally catch up to him. Standing over him were two smaller figures and behind them, two larger ones. Three looked human, the other…

“You shouldn’t have tried to fuck us…” the smaller human grinned with a sinister tone in her voice. “You messed up big time Tony…we could have had a good thing going, but then you tried to fuck us…big mistake.”

“I’m…sorry….I’ll…” He tried to speak, but the knife in his back made it difficult to get the words out.

“Shut him up…make him an example of what happens when you tried to fuck with us…” She ordered her goons with a cold set of red eyes.

With a grin, the other smaller figure lifted his bat up in the air. The last thing that man saw was those red eyes of the leader and the set of horns of the small boy, bringing the wooden bat down on his face.

**Author's Note:**

> Just a heads up! This fic is gonna be a little slow at first but once more and more is established, the story and relationships will pick up and get more intense as it goes on.


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